Antitumor agents, 138. Rotenoids and isoflavones as cytotoxic constitutents from Amorpha fruticosa

J Nat Prod. 1993 May;56(5):690-8. doi: 10.1021/np50095a005.

Abstract

Eight cytotoxic compounds have been isolated from the CHCl3 extract of Amorpha fruticosa. One compound, 6'-O-D-beta-glucopyranosyldalpanol [10], is a new cytotoxic rotenoid. Another known rotenoid, 12 alpha beta-hydroxyamorphigenin [6], was first shown to exhibit extremely potent cytotoxicity (ED50 < 0.001 microgram/ml) in six neoplastic cell lines. In addition to these compounds, three isoflavones (afrormosin [1], 7,2',4', 5'-tetramethoxyisoflavone [2], 8-methylretusin [3]) and five rotenoids (amorphispironone [4], amorphigenin [5], dalpanol [7], 12a beta-hydroxydalpanol [8], and tephrosin [9]) were isolated. Compound 8 was isolated for the first time as a natural product from this plant. The structures of these compounds were established on the basis of spectral data; some were further confirmed by X-ray crystallographic analysis.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Carcinoma, Squamous Cell / drug therapy
  • Drug Screening Assays, Antitumor
  • Humans
  • Isoflavones / chemistry
  • Isoflavones / isolation & purification
  • Isoflavones / pharmacology*
  • Laryngeal Neoplasms / drug therapy
  • Plants, Medicinal / chemistry*
  • Rotenone / analogs & derivatives*
  • Rotenone / chemistry
  • Rotenone / pharmacology*
  • Tumor Cells, Cultured

Substances

  • 7-hydroxy-6,4'-dimethoxyisoflavone
  • Antineoplastic Agents, Phytogenic
  • Isoflavones
  • Rotenone